


Pretty Boys Deserve Pretty Things

by sp1mpi3



Series: We Need to Peg Them All [2]
Category: Shall We Date?: Obey Me!
Genre: Dirty Talk, F/M, Femdom, Pegging, Porn with Feelings, Praise Kink, Stockings, you can't tell me this boy doesn't get pegged
Language: English
Status: Completed
Published: 2020-07-18
Updated: 2020-07-18
Packaged: 2021-03-04 21:47:09
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,171
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25323355
Author URL: https://archiveofourown.org/users/sp1mpi3/pseuds/sp1mpi3
Summary: MC finds some hentai Levi forgot to hide. Turns out, Levi likes being a femboy and making MC happy. It's a good thing he looks good in skirts and stockings.
Relationships: Leviathan (Shall We Date?: Obey Me!)/Original Female Character(s)
Series: We Need to Peg Them All [2]
Series URL: https://archiveofourown.org/series/1919839
Comments: 13
Kudos: 223





	Pretty Boys Deserve Pretty Things

**Author's Note:**

> think I got a little too into writing this. What can I say? I'm a Levi simp who just wants to see him get pegged and praised.

“Levi…?” Levi had told MC she could borrow a manga he had just finished, it was really good and she’s the only other person in this house who would appreciate such good content. He also maybe wanted to have something else to talk about with her. Something that his stupid brothers couldn’t take the spotlight with.   


Without looking away from his game he took his headphones off and answered her, “It should be right in front with the blue cover, it’s called " _Whoa, How Did I Find Myself As the Protagonist of a Harem Manga and How Are They All Going to React When They Find Out I’m Actually the Antagonist of a Shounen Manga?"_ , you can’t miss it.” She was quiet for a moment, and he assumed she had already started reading it. He quickly turned around to look at her face to see if she enjoyed it. Instead, he saw her with a deep blush, looking at hentai. “AH NO PUT THAT BACK DON’T LOOK AT IT!” He scrambled out of his chair to her place on the floor to grab it from her, he must have forgotten to put it on the back shelf last night after he finished it. Panic filled him even more when she moved the book just out of reach so he tripped on his chair and fell fully onto the floor beside her. 

“Why’d you leave it out if you didn’t want me to look at it?” MC may have been blushing, but he could still see the obvious smirk on her face. It was one of the most lewd things he owned. He watched, helpless, as she started to flip through it again. His eyes started to tear up knowing she’d probably make fun of him and tell everyone about how gross their otaku brother really was. Worst of all he just knew MC was going to be so disgusted that she would never hang out with him again.   


MC finally looked up after flipping through it quickly, looking at Levi, her smile dropping, “Levi? What’s wrong?” 

“What’s wrong?!” He gasped, looking up at her with teary eyes, “I just got comfortable having you around and now it’s not fair because you’ve discovered how weird and gross I am and never want to be around me again!” He cried, burying his face in his hands, “Just leave if you’re gonna make fun of me.” 

She set the manga back down, “I was just teasing you a little, I’m sorry.” She reached out to take his hands, gently pulling them from his face. “Look, everyone looks at porn and stuff, yours is just a little uh...different, is all.” 

“If you’re trying to make me feel better, that was a lousy attempt,” he let her keep holding his hands but still didn’t make eye contact. 

“Hey,” she let one of his hands go and touched his face, wiping some tears away, which only made him blush more, “It’s okay. I’m not going to make fun of you or stop hanging out with you because you like to read some stuff.” He found himself leaning into her touch, her hands were always so soft. “Actually, um,” now MC was blushing harder, “it looks kinda...interesting, could I borrow it?” His jaw dropped as he looked at her. Levi was 90% sure he died and was now living out some sick torment of his soul. 

“Are you going to...show it to anyone?” His heart was pounding out of his chest. Do dead demons still feel their heartbeat? 

“Do you really think I’d do that?” she asked. And she had a point, Levi had already entrusted her with secrets, she had more than proved herself an ally, but what if this was the one time she betrayed him. She held up her pinky, “Remember what I told you about us humans? We make pinky promises. They’re the most sacred of oaths.” Finally looking at her, he couldn’t see a trace of malice anywhere on her face or in her eyes. She always had really pretty eyes. 

He groaned and grabbed the hentai from where she laid it down, holding it out to her, “Just take it and go somewhere else to read it.” She smiled at him and carefully took it, “B-But make sure to bring it back when you’re done!” he managed to stutter out as she left to go back to her room. 

That was the day he was sure he would die. Maybe he did die, where do demons go once they die? 

MC had borrowed it on Friday and it was now Sunday, and Levi had spent the entire weekend in a panic and curled under his blankets. He just knew she was disgusted with him. Then he got a text. 

_I finished it!_

He jumped up from his bed and gripped his D.D.D., rereading the text. “Look, Henry, an exclamation point! That’s good right?” He pressed his hand to the glass, watching his pet swim around. “Yeah, you’re right, it could just be in shock. She probably hated it. And now she hates me.” In the middle of his self depreciation, he got a second notification. 

_It was really good. I liked it._

His face was a deeper red than Diavolo’s jacket and he was certain his soul left his body. He looked down at his keyboard and managed to type the only word his shaky hands would let him. 

  
**_Cool._ **

He paced nervously around the room, waiting for another reply. He couldn’t figure out what she meant by “liked it”. Was it out of pity to save his feelings? A bunch of dings came in a row. 

_It was really well written._  
_Thanks for letting me borrow it._  
_Are you into that stuff?_  
_You don’t have to answer that if you don’t want to._  
_That was dumb to ask._  
_Sorry._  
_I’m just curious._  
_I promise I’m not teasing you._  
_Again, thanks for letting me borrow it._  
_I’ll give it back to you tomorrow._  
  
Another one word reply for the win: **Yes.**  
Then he turned his phone off and went to bed, hoping that this was all just some really weird dream and he’d wake up tomorrow never having shared his degenerate shame with MC.

The following day Levi got up and got dressed for the day. Classes, club meetings, student council, and he was in charge of dinner. But all his thoughts of the day were replaced with panic when he opened his door to see a box on the ground. He looked around the hall and didn’t see anyone, so he grabbed it and shut his door again. It was a small brown box with a little note on top. 

  
_Levi,_  
_Thanks again for letting me borrow this. Sorry if I made you uncomfortable, but I’m glad you trust me! I knew you’d probably sleep late so figured it’d be okay to just leave by your room once the others left. Also, to say thank you I added a little gift :) Hope you like it! Have a good day!_  
_MC._

Why did she have to be so cute? He opened the box and saw the hentai neatly on top of some tissue paper. Once he put it back in the secret hiding spot he kept all his private things, he noticed the box still had something in it. Moving the tissue paper, he gasped and dropped the box as if it had burned him. A pair of simple black thigh high stockings. His entire body blushed as he shakily picked them up from the box. They were a soft and stretchy material that made chills go up his spine. The thought crossed his mind to put them on, and then the thought became a chant. He wanted to put them on so badly, to know how they’d feel on his skin. He wanted to show MC. But it was too late to change now, he was already running late for his classes. He cursed at the time and neatly folded them and put them back in the box, hiding it in the back of his closet just in case some idiot decided to come into his room without permission. 

Somehow he managed to get through the day, but it wasn’t easy. He couldn’t stop thinking about that damn box and what was in it. At lunch he caught a glimpse of MC, but she just smiled and waved before leaving. This was torture and dinner was the worst. He ended up burning anything he tried to make, finally he gave up and just ordered some pizzas with the money he was saving to buy the new Ruri-chan figurine. It was MC’s fault, she got him worked up and wasn’t even bothered by it, he just knew she did this to him to mock him. And he had to just sit there and watch as she joked and laughed with his brothers. This world truly wasn’t fair. 

Finally he couldn’t stand it anymore, he quickly got up from his seat at the table, “I’m not feeling well, goodnight,” and left before anyone could say anything to him. He managed to make it back to his room and scrambled to lock the door behind him. Taking a moment to breath, he pulled the box out from hiding. It hadn’t been touched since he put it up this morning, but opening it still made his heart race. Swallowing his pride, he stripped down to his boxers and stood in front of his mirror. He held the stockings up in front of him, imagining what he was going to look like. Blood rushed to his dick as he admired the mirror. Without any gracefulness, he started tugging them onto his legs, hopping on one foot at a time until he got frustrated and sat on the floor. Once both were on, he laid on his back and stared at the ceiling, not ready to look at himself yet. They felt amazing, better than he had ever imagined. He reached down and rubbed from his skin to the sock, feeling the transition of textures and feeling how the elastic at the top was hugging his thighs. His hand reached to palm at his now painfully hard cock, but before he made contact there was a soft knock at the door. “Levi? Are you okay?” He went into full panic mode, jumping up from his lying position and trying to at least find a pair of sweatpants to cover up this shame. “Leviathan?” MC’s voice called from the other side of the door. Hearing her call his name made his erection even worse. 

“H-Hang on,” he managed to call back, tripping over his own feet as he slid into some sweats and a random tshirt on the floor. He took a second to breathe before opening the door, “What?” 

MC stood in the doorway, smiling softly and holding a bowl in her hands, “You said you weren’t feeling well and left dinner before eating anything, so I came to check on you. Even brought you some soup.” 

“I-I don’t want any soup b-but thanks for checking on me-” He started closing the door, but MC stuck her foot in and jammed it so he couldn’t shut it.   


“Unless you were lying to leave early,” she was smirking at him. His breath stopped, he was painfully aware of the fabric of the stockings on his legs. “If that’s the case, I’ll leave you to it. Though, your brothers might get worried and come check on you themselves.” 

He quickly opened the door back up and glanced around the hall. “O-On second thought, soup sounds nice,” and ushered her in. It’s not like she could tell he was wearing them, it just looked like he was wearing black socks. He won’t even mention them, and she’ll never know he was wearing them. Or how much he liked them. Or how much he wanted to thank her and show her what they looked like on him and have her tell him that they look just as amazing as they feel. That would be embarrassing and Levi definitely didn’t feel his dick twitch at the thought of that. 

She smiled again at him and walked in, sitting at his desk and putting the bowl of soup down. She crossed her legs and watched him shut the door. “You’re wearing them, aren’t you?” He froze in place, not looking at her yet. “Well?” His face burned and he slowly turned to meet her gaze. “If you’re honest with me, I might give you the other presents I brought.” He gulped and slowly nodded, still managing to match her stare. Her face lit up with a big smile and she clapped her hands together, “Do you like them? I hope it wasn’t too forward of me to give them to you, but I just couldn’t resist,” MC started rambling and it made Levi relax a little. He had learned that she tends to just keep talking when she’s nervous or excited, it was nice to know he wasn’t the only one totally on edge, and she did seem genuine about giving them to him. He took a few tentative steps closer to her, “and I just sort of kept thinking about all of it and how I wanted those things to happen and then you said you were into it and then I couldn’t stop thinking about you in thigh highs like the main character so I just-” Who knows where it came from, maybe it was the fact that what was left of his pride and ego was already gone or the fact that she was so beautiful and one of the first people to seem truly happy to be near him, but he leaned down and kissed her, cupping his hands on her face. There was a brief moment of panic and dread, but it didn’t take long for her to return the kiss and reach forward to grab his shirt. It wasn’t anything amazing, it was sloppy and exciting, but Levi could have been taken back to the Celestial Realm at that very moment and have no regrets. 

“I like them a-a lot, and I...I like you a lot,” he admitted, still holding her face in his hands because he was worried that if he let go she would leave.   
But she didn’t leave. One hand let go of his shirt and ran through his hair as she smiled at him, “I like you a lot too, Levi. Even if you didn’t like the stockings, I’d still like you,” she kissed his cheek, “...but since you do like them, can I...see them? It’s only fair since I gave them to you…” She gave him her best puppy eyes and he could’ve melted into the floor. He nodded, just wanting to make her happy, and backed up away from the chair. He took a breath and closed his eyes, pulling his shirt and sweatpants off, leaving him in only his boxers and the socks. His eyes shot open when he heard her gasp, she was blushing furiously and staring him up and down. “They’re perfect,” she whispered, filling him with a sense of euphoria and confidence. She snapped out of her trance and gathered her thoughts, “I uh..brought a couple other gifts for you. Here’s one, since it’s kinda silly to wear boxers with them,” She reached into her bag and pulled out a piece of clothing and handed it to him. He unfolded it and bit his lip, a short black skirt. 

“I-I don’t know what to say, it’s...soft…” he ran his thumbs across the fabric, it was soft like the stockings. 

“Do you wanna wear it?” He nodded eagerly. She spun the chair around so her back was to him, “Go ahead, I promise I won’t look until you want me to.” That took a bit of pressure off of him, he didn’t have to focus on looking majestic while figuring out how to put on a damn skirt. 

When he slid his boxers off, he was immediately reminded of how hard he was. His dick was red and leaking, but he knew if he could hold out a little longer it’d be so worth it. Somehow finding the willpower to not jerk it right there, he figured out that the skirt was a simple slip on. “O-Okay, you can look now.” 

Levi stood in front of the mirror, now wearing a skirt to match his stockings. “Such a pretty boy,” MC praised behind him, her arms rubbing his shoulders as she stared in the mirror with him. His hands balled into fists as he gripped the fabric of the skirt that barely gave him any cover and was obviously tented from his erection. MC stood on her toes to get up to his ear, “There’s still one last gift you need to open,” she whispered, stepping back to grab another box from her bag and handed it to him. His hands shook as he took the lid off. He gasped looking at the contents. “Do you like it? In all honesty, I finished reading it the night you let me borrow it. I spent the rest of the weekend ordering some stuff I thought you’d like.” Inside the box was a large, dark blue dildo and an accompanying harness. “I know it’s not real like the girls in the hentai, but I suppose this is the next best thing.” She looked up at him, waiting for his approval, but all he could do was stare at it. “Leviathan,” her voice snapped him out of it as he made eye contact with her through the mirror, “What do you say when someone gives you a gift you like?”   


He was sure he hadn’t stopped blushing since the first minute she found his hentai, but somehow it darkened and he spun around to look at the real MC, “Thank you, thank you very much.” 

Her hand followed a line up his chest and rested under his chin, “You deserve it.” Her other hand slowly was running under the bottom of his skirt. “My sweet boy deserves the best,” she cooed, his dick jumped at that. Her hand slid under what little of the fabric was covering him, and groped his ass. His breath hitched, but in a good way. He couldn’t decide which hand he wanted to lean into more. The box holding the strap was still tightly in his grasp as he enjoyed the barrage of affection MC was giving him, until everything stopped and she gently took the box. Wordlessly, she led him over to his bed and motioned for him to sit. 

“MC..?” He asked quietly, looking up at her. 

“Yes, my pretty little boy?” His heart swelled when she called him that. She gently ran her fingers through his hair. 

“Do you...do you really think I look pretty?” His voice was almost a whisper. 

She brushed his bangs back out from his eyes and smiled at him, “You’re the prettiest thing I’ve ever seen,” and kissed his forehead. “In fact, let me show you something,” she stepped as close as she could be and took his hand, guiding it under the skirt of her RAD uniform. He gasped when she pressed his fingers against her underwear, “This is because of you.” He bit down on his lip and moved his fingers, not entirely sure of what he was doing but pressing and feeling to get a reaction from her. She let out a soft moan and tightened her grip on his wrist, “Levi…” Hearing his name come from her lips was almost enough to get him to cum right then. He doubled his efforts to figure out what felt good for her and went with the motion of her hips as she started to grind down on his hand. One hand holding his wrist, the other his shoulder to anchor her so that she wouldn’t fall when her knees gave out. A string of short moans echoed through his room while she humped his hand, until her hips stuttered and she froze, softly panting.

Her hand guided his back out from under her skirt and up to his face, in front of his mouth. He slowly opened and sucked on his own fingers, she tasted sweet. Once she was satisfied watching him do that, but gently pushed him back onto the back and straddled his abdomen, “Such a sweet boy, making me feel good. So considerate and kind.” His hips jutted up at the praise, if he tried hard enough he could almost get some sort of contact. She hummed softly, letting her hands roam the expanse of his chest, stopping briefly to run her thumbs over his sensitive nipples. Levi moaned surprisingly loud when she bit down on his collar bone. “Wanna mark you up,” she spoke against his skin, kissing and sucking up his neck, “Can I? Do you wanna be my pretty boy?” She ended the question with a playful nip to his jaw and sat up, looking down at him again.

He gets to feel nice, be hers, and get this view of being below MC? If she asked him to kill Lucifer right now he could probably do it. “Am I...your favorite?” He shyly asked.

The question made her chuckle softly and give him a small kiss on the lips, “Definitely. You’re the only boy I want.” She shuffled around on top of him a bit until he whined, feeling the pressure of her thigh against his painfully hard dick. “Want you to cum for me in your pretty skirt, Levi, show me how much you appreciate my gift,” she pressed her thigh against his groin again and that was all the permission he needed before frantically humping her leg, like a dog in heat. He reached out and grabbed her hips, a bit in fear she would leave him but mostly because he needed the contact with her skin, to make sure she was real. It didn’t take long for him to reach his peak, cumming all over the front of his new skirt, digging his fingertips into her hips and letting out a string of moans and her name. They stayed like that for a moment so he could catch his breath, she gently pet his head and told him he was such a good boy.

He struggled to catch his breath and opened his eyes to see her still above him, smiling so beautifully like an angel. He got to see her like this, not Mammon or Lucifer or any of his brothers, she only wanted to do this with him. He grinned back up at her and she kissed his lips, “You have a nice smile.”

“Thank you,” he managed to get out, which made her smile more.

“Is my good boy okay to try something else?” His dick perked up at the question, “I’ll take that as a yes,” she giggled and carefully climbed off of him. He watched as she effortlessly slipped her clothes off, he couldn’t believe MC was standing in his room in only her bra and underwear, dreams kept coming true.  


“Wanna touch-” he breathed out, reaching for her.

“You’ll get to, I promise. You just have to be patient.” She retrieved the box he had yet to forget about and turned her back to him. He stared at her, swearing to himself that he’d remember every curve she had, every detail of her body down to the last freckle. He watched her shimmy into the simple harness and get comfortable, then assumed she was fixing the dildo. He felt more blood rush from his head back to his dick. He honestly shouldn’t be able to get hard again this fast, but he wasn’t complaining. She turned back around and a whine left the back of his throat, the strap was a stark contrast to her body and the dildo was bigger than would fit her body type, but he was already so excited, and so was she. MC saw him staring and ran her hand along her fake dick, “Do you like it?” He nodded. “Can you flip over for me, sweet boy?” He managed to sit up and turn over, propping himself on his knees and letting his shoulders rest on the pillows below. His whole body was trembling with nerves and excitement.

He jumped a bit when he felt her hands touch his back, but it didn’t take long for him to relax again and melt into her touch. “Be a good boy for me, okay? Good boys speak up if they want to stop or don’t like something.” Her hands rubbed circles on the small of his back, making chills rise on his skin. “Good boys also say if they like what’s happening and what they want.”

“Please,” he mumbled, hands gripping the pillow under his head, “I-I want it, MC, please, wanna be good,” tears were already starting to prick his eyes with how much he wanted this.

MC rewarded him with a playful kiss on his hip, “We’re gonna go slow, okay? It’s gonna be cold and a little uncomfortable, but I know my sweet boy can do it.” He moaned into the pillow, the affirmations going straight to his hard cock. She pushed the skirt so it was bunched up at his waist, leaving him feeling completely exposed. There was a soft pop as she opened a bottle and he felt a hand on his ass again. He whined when he felt her now wet finger trace around the rim of his asshole, just barely applying pressure, “Gotta relax for me, sweetheart, I promise it’ll feel good.” He took some quick breaths and willed his body to relax, a choked moan coming from his chest when he felt the tip of her finger push past his muscle. She hummed and rubbed her thumb in small circles on his hip, “Doing so well for me.”

He relaxed more and her finger slid further inside of him. She gave him a moment to get used to it before shallowly thrusting it in and out. Once he started to push his hips back to meet her hand, she carefully added a second. He mewled at the intrusion and the slight burn the stretch gave, but it wasn’t a bad feeling, especially when she curled her fingers and pressed against his prostate, “A-Ah!” He cried out when she did it a second time. She planted a soft kiss on his back and kept going, scissoring her fingers to stretch him and occasionally grazing his prostate which made him moan and lean further back into her touch. Carefully she pulled her fingers out and wiped the remaining lube on her dildo. Levi whined at the feeling of being empty, “Want more, please~”

“Shh,” MC peppered a trail of kisses up his spine, “I’m gonna take care of you, baby boy.” His dick leaked and he moaned softly into the pillow, he would come again from her words alone if she kept this up. He heard a bottle being opened again as she generously coated the strap. He felt the top of it tease him, lightly brushing over his twitching hole, “Remember what I said about good boys? They speak up when they want something.”

“Nnh,” he groaned, fighting back the urge to cry, “Want you, want you to make me feel good, please, wanna be good!” He took a sharp breath when she started pushing the dildo. He gripped the pillow tighter, nails almost ripping the fabric, but she went slow and easy, letting him get used to it a little at a time. Finally, he felt her hips press against his backside and impossibly full.

“Are you okay?” Her concern broke through the haze in his mind, but all he could do was grunt and nod. “Doing so well, took my whole cock,” she pulled back about an inch, and thrust back in. He shot up onto his hand and cried out, not expecting the jolt of pleasure to go up his spine. “Levi? Do you want to stop?” She sounded so concerned as he hung his head and started panting. 

“N-No,” he said, “Just felt really good.” There was no way he was going to ask to stop this, it was a dream come true. She chuckled behind him and thrust her hips again, and again, until she built up a steady rhythm, each thrust rubbing his prostate and pushing moans and whines from his mouth. “Wait!” 

She immediately stopped and leaned over him, “What is it, sweetheart?” His face was red and tear streaked, 

“Wanna..wanna look at you,” he admitted shyly. She kissed the spot between his shoulder blades and eased out of him. After a bit of maneuvering, she was sitting up on the bed with Levi in her lap. They kissed as he straddled her, getting impatient and sinking down quickly, his moans muffled against MC’s lips. His hands roamed what felt like an infinite expanse of her skin, she was soft and warm and so close, “MC…” he whined against her, wildly bouncing in her lap as he chased his second orgasm. 

“You look so perfect like this, Levi,” she held onto his hips to keep him from falling and to try to get him into some sort of rhythm, “Such a beautiful boy, built to take my dick,” her face nuzzled into the crook of his neck. The pitch of his moans got higher as more tears streamed down his cheeks, he had never dreamed it would feel so good to let someone take him, didn’t even think that MC would be willing to take him. But now he can’t imagine ever going back to an existence where he didn’t have her warm breath on his neck and her hands on his hips. Sinking down on the full length of her cock, he threw his head back and choked out one final moan, cumming harder than he ever had in his life, fireworks going off in his brain as he rode out his orgasm. 

The rest was a blur to him. MC carefully lifted him up and down onto his bed, stripping off the stained clothes and cleaning both him and her up, before laying down and pulling him close to cuddle. “Still with me, Levi?” 

“Yeah,” he hummed, wrapping his arms around her tightly. Tomorrow he would have to make up some excuse about why he wasn’t able to leave his room or why someone may have heard sounds coming from his room or why he was probably walking funny or even why MC was staying with him, but that was all problems for tomorrow. But tonight, Levi wouldn’t let this high fade. “Thank you,” he mumbled before dozing off.


End file.
